The 9,10-anthraquinone ring system of the title compound, C
25H
26O
5, is essentially planar. The
O-geranyl substituent is at the
meta position with respect to the hydroxyl group. O—H
O intramolecular hydrogen bonds are observed in the molecular structure. The molecules form centrosymmetric hydrogen-bonded dimers
via intermolecular C—H
O hydrogen bonds which generate rings of motif
R22(10). The crystal structure is further stabilized by weak π–π interactions.
Supporting information
CCDC reference: 264064
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.005 Å
- R factor = 0.086
- wR factor = 0.219
- Data-to-parameter ratio = 13.4
checkCIF/PLATON results
No syntax errors found
Alert level B
PLAT230_ALERT_2_B Hirshfeld Test Diff for O3 - C10 .. 11.19 su
PLAT242_ALERT_2_B Check Low Ueq as Compared to Neighbors for C21
Alert level C
PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 3.43 Ratio
PLAT222_ALERT_3_C Large Non-Solvent H Ueq(max)/Ueq(min) ... 3.74 Ratio
PLAT230_ALERT_2_C Hirshfeld Test Diff for C21 - C22 .. 5.15 su
PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C20
PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C17
PLAT333_ALERT_2_C Large Average Benzene C-C Dist. C5 -C10 1.45 Ang.
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 6
0 ALERT level A = In general: serious problem
2 ALERT level B = Potentially serious problem
7 ALERT level C = Check and explain
0 ALERT level G = General alerts; check
0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
7 ALERT type 2 Indicator that the structure model may be wrong or deficient
2 ALERT type 3 Indicator that the structure quality may be low
0 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 1997); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2003).
3-(3,7-Dimethylocta-2,6-dienyloxy)-1,8-dihydroxy-6-methyl-9,10-anthraquinone
top
Crystal data top
C25H26O5 | Z = 2 |
Mr = 406.46 | F(000) = 432 |
Triclinic, P1 | Dx = 1.279 Mg m−3 |
Hall symbol: -P 1 | Melting point = 391–392 K |
a = 4.6082 (1) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 12.965 (4) Å | Cell parameters from 1719 reflections |
c = 18.105 (5) Å | θ = 1.0–28.1° |
α = 100.074 (5)° | µ = 0.09 mm−1 |
β = 92.978 (5)° | T = 293 K |
γ = 96.526 (5)° | Needle, orange |
V = 1055.3 (4) Å3 | 0.28 × 0.05 × 0.05 mm |
Data collection top
Siemens SMART CCD area-detector diffractometer | 3693 independent reflections |
Radiation source: fine-focus sealed tube | 2097 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.044 |
Detector resolution: 8.33 pixels mm-1 | θmax = 25.0°, θmin = 1.8° |
ω scans | h = −5→5 |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | k = −15→15 |
Tmin = 0.995, Tmax = 0.996 | l = −21→21 |
9919 measured reflections | |
Refinement top
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.086 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.219 | H-atom parameters constrained |
S = 1.07 | w = 1/[σ2(Fo2) + (0.0885P)2 + 0.4977P] where P = (Fo2 + 2Fc2)/3 |
3693 reflections | (Δ/σ)max < 0.001 |
275 parameters | Δρmax = 0.22 e Å−3 |
0 restraints | Δρmin = −0.21 e Å−3 |
Special details top
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell e.s.d.'s are taken
into account individually in the estimation of e.s.d.'s in distances, angles
and torsion angles; correlations between e.s.d.'s in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s.
planes. |
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor
wR and goodness of fit S are based on F2, conventional
R-factors R are based on F, with F set to zero for
negative F2. The threshold expression of F2 >
σ(F2) is used only for calculating R-factors(gt) etc.
and is not relevant to the choice of reflections for refinement.
R-factors based on F2 are statistically about twice as large
as those based on F, and R- factors based on ALL data will be
even larger. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
O1 | −0.5595 (7) | 0.1811 (2) | −0.28870 (14) | 0.0808 (10) | |
H1 | −0.4258 | 0.2281 | −0.2721 | 0.121* | |
O2 | −0.1919 (5) | 0.2991 (2) | −0.18760 (13) | 0.0596 (8) | |
O3 | −0.6424 (6) | 0.1018 (2) | 0.02578 (15) | 0.0735 (9) | |
O4 | 0.1972 (5) | 0.41094 (18) | −0.09103 (13) | 0.0544 (7) | |
H4 | 0.1095 | 0.3898 | −0.1325 | 0.082* | |
O5 | 0.1842 (5) | 0.34737 (19) | 0.15961 (13) | 0.0561 (7) | |
C1 | −0.6553 (8) | 0.1338 (3) | −0.2325 (2) | 0.0542 (10) | |
C2 | −0.8819 (8) | 0.0511 (3) | −0.2500 (2) | 0.0592 (11) | |
H2 | −0.9633 | 0.0320 | −0.2993 | 0.071* | |
C3 | −0.9887 (8) | −0.0031 (3) | −0.1965 (2) | 0.0495 (9) | |
C4 | −0.8717 (7) | 0.0282 (3) | −0.1226 (2) | 0.0450 (9) | |
H4A | −0.9455 | −0.0068 | −0.0857 | 0.054* | |
C5 | −0.6486 (7) | 0.1102 (3) | −0.10327 (19) | 0.0405 (8) | |
C6 | −0.5319 (7) | 0.1649 (3) | −0.15817 (19) | 0.0432 (9) | |
C7 | −0.2916 (7) | 0.2510 (3) | −0.1378 (2) | 0.0427 (9) | |
C8 | −0.1669 (7) | 0.2788 (2) | −0.06126 (18) | 0.0385 (8) | |
C9 | −0.2770 (7) | 0.2259 (2) | −0.00469 (19) | 0.0371 (8) | |
C10 | −0.5303 (7) | 0.1413 (3) | −0.02410 (19) | 0.0418 (9) | |
C11 | −0.1556 (7) | 0.2514 (3) | 0.06733 (19) | 0.0422 (9) | |
H11 | −0.2311 | 0.2160 | 0.1039 | 0.051* | |
C12 | 0.0821 (7) | 0.3308 (3) | 0.08654 (19) | 0.0428 (9) | |
C13 | 0.1932 (7) | 0.3849 (3) | 0.0330 (2) | 0.0434 (9) | |
H13 | 0.3480 | 0.4388 | 0.0462 | 0.052* | |
C14 | 0.0732 (7) | 0.3585 (2) | −0.04039 (19) | 0.0388 (8) | |
C15 | 0.4333 (8) | 0.4258 (3) | 0.1864 (2) | 0.0544 (10) | |
H15A | 0.3738 | 0.4960 | 0.1943 | 0.065* | |
H15B | 0.5811 | 0.4225 | 0.1501 | 0.065* | |
C16 | 0.5495 (8) | 0.4014 (3) | 0.2577 (2) | 0.0548 (10) | |
H16 | 0.6283 | 0.3379 | 0.2540 | 0.066* | |
C17 | 0.5570 (9) | 0.4573 (3) | 0.3259 (2) | 0.0630 (11) | |
C18 | 0.6733 (11) | 0.4216 (4) | 0.3946 (2) | 0.0799 (14) | |
H18A | 0.5173 | 0.4188 | 0.4284 | 0.096* | |
H18B | 0.8278 | 0.4753 | 0.4196 | 0.096* | |
C19 | 0.7924 (11) | 0.3171 (4) | 0.3844 (2) | 0.0851 (15) | |
H19A | 0.6444 | 0.2629 | 0.3568 | 0.102* | |
H19B | 0.9607 | 0.3207 | 0.3545 | 0.102* | |
C20 | 0.8810 (12) | 0.2864 (4) | 0.4569 (3) | 0.0998 (18) | |
H20 | 1.0108 | 0.3364 | 0.4893 | 0.120* | |
C21 | 0.8032 (10) | 0.1998 (4) | 0.4814 (2) | 0.0741 (13) | |
C22 | 0.5917 (16) | 0.1116 (4) | 0.4367 (3) | 0.127 (2) | |
H22A | 0.5066 | 0.1348 | 0.3939 | 0.191* | |
H22B | 0.4398 | 0.0916 | 0.4677 | 0.191* | |
H22C | 0.6932 | 0.0521 | 0.4200 | 0.191* | |
C23 | 0.9084 (14) | 0.1792 (5) | 0.5568 (3) | 0.116 (2) | |
H23A | 1.0404 | 0.2389 | 0.5825 | 0.174* | |
H23B | 1.0083 | 0.1176 | 0.5500 | 0.174* | |
H23C | 0.7440 | 0.1682 | 0.5862 | 0.174* | |
C24 | −1.2268 (9) | −0.0953 (3) | −0.2176 (2) | 0.0654 (12) | |
H24A | −1.3521 | −0.0841 | −0.2587 | 0.098* | |
H24B | −1.3399 | −0.1015 | −0.1751 | 0.098* | |
H24C | −1.1401 | −0.1590 | −0.2323 | 0.098* | |
C25 | 0.4357 (15) | 0.5620 (4) | 0.3414 (3) | 0.114 (2) | |
H25A | 0.2781 | 0.5622 | 0.3046 | 0.171* | |
H25B | 0.5877 | 0.6181 | 0.3387 | 0.171* | |
H25C | 0.3643 | 0.5722 | 0.3907 | 0.171* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.097 (2) | 0.098 (2) | 0.0436 (17) | −0.0224 (18) | −0.0083 (15) | 0.0274 (16) |
O2 | 0.0689 (17) | 0.0657 (18) | 0.0465 (16) | −0.0068 (14) | 0.0046 (13) | 0.0258 (14) |
O3 | 0.078 (2) | 0.076 (2) | 0.0629 (19) | −0.0107 (16) | 0.0085 (15) | 0.0145 (16) |
O4 | 0.0631 (16) | 0.0506 (15) | 0.0509 (16) | −0.0098 (12) | 0.0073 (12) | 0.0229 (12) |
O5 | 0.0621 (16) | 0.0582 (16) | 0.0421 (16) | −0.0142 (13) | −0.0028 (12) | 0.0089 (12) |
C1 | 0.055 (2) | 0.066 (3) | 0.045 (2) | 0.009 (2) | 0.0024 (19) | 0.019 (2) |
C2 | 0.061 (2) | 0.066 (3) | 0.047 (2) | 0.005 (2) | −0.0127 (19) | 0.005 (2) |
C3 | 0.046 (2) | 0.048 (2) | 0.055 (3) | 0.0103 (17) | 0.0006 (18) | 0.0091 (19) |
C4 | 0.044 (2) | 0.043 (2) | 0.049 (2) | 0.0057 (16) | 0.0061 (17) | 0.0092 (17) |
C5 | 0.0401 (19) | 0.040 (2) | 0.043 (2) | 0.0117 (16) | 0.0056 (16) | 0.0071 (16) |
C6 | 0.046 (2) | 0.047 (2) | 0.041 (2) | 0.0109 (17) | 0.0057 (17) | 0.0127 (17) |
C7 | 0.048 (2) | 0.041 (2) | 0.044 (2) | 0.0098 (16) | 0.0112 (17) | 0.0162 (17) |
C8 | 0.0393 (19) | 0.0357 (19) | 0.044 (2) | 0.0102 (15) | 0.0094 (16) | 0.0113 (16) |
C9 | 0.0380 (18) | 0.0340 (19) | 0.042 (2) | 0.0090 (15) | 0.0078 (15) | 0.0106 (15) |
C10 | 0.045 (2) | 0.043 (2) | 0.043 (2) | 0.0032 (16) | 0.0166 (17) | 0.0177 (17) |
C11 | 0.045 (2) | 0.041 (2) | 0.042 (2) | 0.0040 (16) | 0.0072 (17) | 0.0119 (16) |
C12 | 0.044 (2) | 0.043 (2) | 0.042 (2) | 0.0064 (16) | 0.0049 (17) | 0.0071 (17) |
C13 | 0.042 (2) | 0.0345 (19) | 0.054 (2) | 0.0007 (15) | 0.0055 (17) | 0.0110 (17) |
C14 | 0.0418 (19) | 0.0329 (19) | 0.046 (2) | 0.0067 (15) | 0.0090 (16) | 0.0144 (16) |
C15 | 0.060 (2) | 0.046 (2) | 0.053 (2) | −0.0041 (18) | −0.0031 (19) | 0.0080 (18) |
C16 | 0.067 (3) | 0.044 (2) | 0.051 (3) | −0.0023 (18) | −0.0062 (19) | 0.0113 (19) |
C17 | 0.080 (3) | 0.051 (3) | 0.050 (3) | −0.010 (2) | −0.005 (2) | 0.005 (2) |
C18 | 0.104 (4) | 0.075 (3) | 0.051 (3) | −0.013 (3) | −0.016 (2) | 0.008 (2) |
C19 | 0.111 (4) | 0.076 (3) | 0.063 (3) | −0.011 (3) | −0.021 (3) | 0.021 (3) |
C20 | 0.130 (5) | 0.092 (4) | 0.067 (3) | −0.023 (3) | −0.041 (3) | 0.023 (3) |
C21 | 0.092 (3) | 0.076 (3) | 0.057 (3) | 0.015 (3) | 0.000 (2) | 0.019 (2) |
C22 | 0.184 (7) | 0.096 (4) | 0.100 (4) | −0.006 (4) | −0.010 (4) | 0.035 (4) |
C23 | 0.159 (6) | 0.128 (5) | 0.070 (4) | 0.025 (4) | −0.007 (3) | 0.040 (3) |
C24 | 0.061 (3) | 0.060 (3) | 0.069 (3) | −0.002 (2) | −0.007 (2) | 0.005 (2) |
C25 | 0.186 (6) | 0.080 (4) | 0.072 (4) | 0.031 (4) | 0.000 (4) | −0.005 (3) |
Geometric parameters (Å, º) top
O1—C1 | 1.346 (4) | C15—C16 | 1.470 (5) |
O1—H1 | 0.82 | C15—H15A | 0.97 |
O2—C7 | 1.260 (4) | C15—H15B | 0.97 |
O3—C10 | 1.223 (4) | C16—C17 | 1.314 (5) |
O4—C14 | 1.346 (3) | C16—H16 | 0.93 |
O4—H4 | 0.82 | C17—C18 | 1.496 (6) |
O5—C12 | 1.353 (4) | C17—C25 | 1.513 (6) |
O5—C15 | 1.446 (4) | C18—C19 | 1.504 (6) |
C1—C2 | 1.390 (5) | C18—H18A | 0.97 |
C1—C6 | 1.405 (5) | C18—H18B | 0.97 |
C2—C3 | 1.372 (5) | C19—C20 | 1.486 (6) |
C2—H2 | 0.93 | C19—H19A | 0.97 |
C3—C4 | 1.390 (5) | C19—H19B | 0.97 |
C3—C24 | 1.509 (5) | C20—C21 | 1.299 (6) |
C4—C5 | 1.375 (4) | C20—H20 | 0.93 |
C4—H4A | 0.93 | C21—C22 | 1.500 (7) |
C5—C6 | 1.413 (4) | C21—C23 | 1.502 (6) |
C5—C10 | 1.477 (5) | C22—H22A | 0.96 |
C6—C7 | 1.463 (5) | C22—H22B | 0.96 |
C7—C8 | 1.441 (5) | C22—H22C | 0.96 |
C8—C14 | 1.413 (4) | C23—H23A | 0.96 |
C8—C9 | 1.413 (4) | C23—H23B | 0.96 |
C9—C11 | 1.361 (5) | C23—H23C | 0.96 |
C9—C10 | 1.490 (4) | C24—H24A | 0.96 |
C11—C12 | 1.399 (5) | C24—H24B | 0.96 |
C11—H11 | 0.93 | C24—H24C | 0.96 |
C12—C13 | 1.380 (4) | C25—H25A | 0.96 |
C13—C14 | 1.382 (5) | C25—H25B | 0.96 |
C13—H13 | 0.93 | C25—H25C | 0.96 |
| | | |
C1—O1—H1 | 109.5 | H15A—C15—H15B | 108.6 |
C14—O4—H4 | 109.5 | C17—C16—C15 | 128.7 (4) |
C12—O5—C15 | 119.9 (3) | C17—C16—H16 | 115.6 |
O1—C1—C2 | 117.8 (3) | C15—C16—H16 | 115.6 |
O1—C1—C6 | 122.0 (3) | C16—C17—C18 | 123.4 (4) |
C2—C1—C6 | 120.1 (3) | C16—C17—C25 | 122.1 (4) |
C3—C2—C1 | 121.8 (3) | C18—C17—C25 | 114.4 (4) |
C3—C2—H2 | 119.1 | C17—C18—C19 | 117.9 (4) |
C1—C2—H2 | 119.1 | C17—C18—H18A | 107.8 |
C2—C3—C4 | 118.6 (3) | C19—C18—H18A | 107.8 |
C2—C3—C24 | 120.7 (3) | C17—C18—H18B | 107.8 |
C4—C3—C24 | 120.7 (3) | C19—C18—H18B | 107.8 |
C5—C4—C3 | 121.1 (3) | H18A—C18—H18B | 107.2 |
C5—C4—H4A | 119.4 | C20—C19—C18 | 113.0 (4) |
C3—C4—H4A | 119.4 | C20—C19—H19A | 109.0 |
C4—C5—C6 | 120.8 (3) | C18—C19—H19A | 109.0 |
C4—C5—C10 | 119.6 (3) | C20—C19—H19B | 109.0 |
C6—C5—C10 | 119.7 (3) | C18—C19—H19B | 109.0 |
C1—C6—C5 | 117.6 (3) | H19A—C19—H19B | 107.8 |
C1—C6—C7 | 121.6 (3) | C21—C20—C19 | 129.3 (5) |
C5—C6—C7 | 120.8 (3) | C21—C20—H20 | 115.3 |
O2—C7—C8 | 120.5 (3) | C19—C20—H20 | 115.3 |
O2—C7—C6 | 119.8 (3) | C20—C21—C22 | 122.2 (4) |
C8—C7—C6 | 119.7 (3) | C20—C21—C23 | 123.8 (5) |
C14—C8—C9 | 117.6 (3) | C22—C21—C23 | 113.9 (4) |
C14—C8—C7 | 121.2 (3) | C21—C22—H22A | 109.5 |
C9—C8—C7 | 121.2 (3) | C21—C22—H22B | 109.5 |
C11—C9—C8 | 120.9 (3) | H22A—C22—H22B | 109.5 |
C11—C9—C10 | 119.6 (3) | C21—C22—H22C | 109.5 |
C8—C9—C10 | 119.5 (3) | H22A—C22—H22C | 109.5 |
O3—C10—C5 | 121.3 (3) | H22B—C22—H22C | 109.5 |
O3—C10—C9 | 119.7 (3) | C21—C23—H23A | 109.5 |
C5—C10—C9 | 119.0 (3) | C21—C23—H23B | 109.5 |
C9—C11—C12 | 120.3 (3) | H23A—C23—H23B | 109.5 |
C9—C11—H11 | 119.9 | C21—C23—H23C | 109.5 |
C12—C11—H11 | 119.9 | H23A—C23—H23C | 109.5 |
O5—C12—C13 | 125.3 (3) | H23B—C23—H23C | 109.5 |
O5—C12—C11 | 114.3 (3) | C3—C24—H24A | 109.5 |
C13—C12—C11 | 120.4 (3) | C3—C24—H24B | 109.5 |
C12—C13—C14 | 119.6 (3) | H24A—C24—H24B | 109.5 |
C12—C13—H13 | 120.2 | C3—C24—H24C | 109.5 |
C14—C13—H13 | 120.2 | H24A—C24—H24C | 109.5 |
O4—C14—C13 | 117.2 (3) | H24B—C24—H24C | 109.5 |
O4—C14—C8 | 121.7 (3) | C17—C25—H25A | 109.5 |
C13—C14—C8 | 121.2 (3) | C17—C25—H25B | 109.5 |
O5—C15—C16 | 106.6 (3) | H25A—C25—H25B | 109.5 |
O5—C15—H15A | 110.4 | C17—C25—H25C | 109.5 |
C16—C15—H15A | 110.4 | H25A—C25—H25C | 109.5 |
O5—C15—H15B | 110.4 | H25B—C25—H25C | 109.5 |
C16—C15—H15B | 110.4 | | |
| | | |
O1—C1—C2—C3 | 178.5 (3) | C4—C5—C10—C9 | 176.4 (3) |
C6—C1—C2—C3 | −0.9 (6) | C6—C5—C10—C9 | −3.8 (5) |
C1—C2—C3—C4 | 2.0 (6) | C11—C9—C10—O3 | 6.0 (5) |
C1—C2—C3—C24 | −177.6 (4) | C8—C9—C10—O3 | −173.6 (3) |
C2—C3—C4—C5 | −1.6 (5) | C11—C9—C10—C5 | −176.5 (3) |
C24—C3—C4—C5 | 178.1 (3) | C8—C9—C10—C5 | 3.9 (5) |
C3—C4—C5—C6 | 0.0 (5) | C8—C9—C11—C12 | −0.2 (5) |
C3—C4—C5—C10 | 179.9 (3) | C10—C9—C11—C12 | −179.9 (3) |
O1—C1—C6—C5 | 179.9 (3) | C15—O5—C12—C13 | −1.4 (5) |
C2—C1—C6—C5 | −0.6 (5) | C15—O5—C12—C11 | 178.7 (3) |
O1—C1—C6—C7 | 0.0 (6) | C9—C11—C12—O5 | −179.2 (3) |
C2—C1—C6—C7 | 179.4 (3) | C9—C11—C12—C13 | 0.9 (5) |
C4—C5—C6—C1 | 1.1 (5) | O5—C12—C13—C14 | 178.4 (3) |
C10—C5—C6—C1 | −178.8 (3) | C11—C12—C13—C14 | −1.7 (5) |
C4—C5—C6—C7 | −179.0 (3) | C12—C13—C14—O4 | −177.4 (3) |
C10—C5—C6—C7 | 1.1 (5) | C12—C13—C14—C8 | 1.7 (5) |
C1—C6—C7—O2 | 0.3 (5) | C9—C8—C14—O4 | 178.1 (3) |
C5—C6—C7—O2 | −179.6 (3) | C7—C8—C14—O4 | −0.7 (5) |
C1—C6—C7—C8 | −178.6 (3) | C9—C8—C14—C13 | −1.0 (5) |
C5—C6—C7—C8 | 1.5 (5) | C7—C8—C14—C13 | −179.8 (3) |
O2—C7—C8—C14 | −1.5 (5) | C12—O5—C15—C16 | −161.6 (3) |
C6—C7—C8—C14 | 177.4 (3) | O5—C15—C16—C17 | −114.2 (4) |
O2—C7—C8—C9 | 179.8 (3) | C15—C16—C17—C18 | 177.9 (4) |
C6—C7—C8—C9 | −1.4 (5) | C15—C16—C17—C25 | 0.4 (7) |
C14—C8—C9—C11 | 0.2 (5) | C16—C17—C18—C19 | 1.1 (7) |
C7—C8—C9—C11 | 179.0 (3) | C25—C17—C18—C19 | 178.7 (4) |
C14—C8—C9—C10 | 179.9 (3) | C17—C18—C19—C20 | −175.7 (4) |
C7—C8—C9—C10 | −1.3 (5) | C18—C19—C20—C21 | 126.5 (6) |
C4—C5—C10—O3 | −6.2 (5) | C19—C20—C21—C22 | −1.0 (10) |
C6—C5—C10—O3 | 173.7 (3) | C19—C20—C21—C23 | −179.4 (5) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1···O2 | 0.82 | 1.86 | 2.583 (4) | 146 |
O4—H4···O2 | 0.82 | 1.84 | 2.563 (3) | 146 |
C4—H4A···O3i | 0.93 | 2.54 | 3.393 (5) | 153 |
Symmetry code: (i) −x−2, −y, −z. |